Triphenylphosphine → HCID 88116714, compound

HRID 395593Notes

Reaction equation

HRID 395593 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][OH:43])=[CH:37][CH:36]=1.[C:44](O)(=[S:46])[CH3:45]>O1CCCC1>[C:44]([O:43][CH2:42][CH2:41][C:38]1[CH:39]=[CH:40][C:35]([Br:34])=[CH:36][CH:37]=1)(=[S:46])[CH3:45]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 728512-(4-Bromophenyl)ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 88116714HCID 88116714, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 mmol (1 ml) of DIAD are added to a solution, cooled to 0° C., of 5 mmol (1.32 g) of triphenylphosphine in 16 ml of tetrahydrofuran. After stirring the mixture cold for 15 minutes, there is added dropwise thereto a mixture of 2.5 mmol (0.5 g) of 2-(4-bromophenyl)-1-ethanol and 5 mmol (0.83 ml) of thioacetic acid diluted with 5 ml of tetrahydrofuran. The mixture is stirred cold for a further 10 minutes and then the temperature is brought to ambient temperature for 18 hours. The solvents are evaporated off. The residue is taken up in diisopropyl ether and the precipitate formed is filtered off. The filtrate is concentrated and then purified by chromatography on silica gel. using petroleum ether as eluant, to yield the expected product.

Workup

  1. additionthere is added dropwise
  2. stirringThe mixture is stirred cold for a further 10 minutes
  3. waitthe temperature is brought to ambient temperature for 18 hours
  4. customThe solvents are evaporated off
  5. customthe precipitate formed
  6. filtrationis filtered off
  7. concentrationThe filtrate is concentrated
  8. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-10276dc3ac66454bb9f8c57404e8ba74
Source dataset
uspto-grants-2003_08
Patent number
US06605604B1

Reaction notes

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